Triethylamine → HCID 66899075, Verbindung

HRID 384235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384235
[F:1][C:2]1[CH:3]=[C:4]([C:9]#[N:10])[CH:5]=[C:6]([CH:8]=1)[NH2:7].O=C(Cl)[O:13][C:14](Cl)(Cl)Cl.C(N(CC)CC)C.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=1[F:37]>O1CCCC1.O>[F:37][C:28]1[CH:29]=[C:30]([C:33]([F:35])([F:36])[F:34])[CH:31]=[CH:32][C:27]=1[NH:26][C:14]([NH:7][C:6]1[CH:8]=[C:2]([F:1])[CH:3]=[C:4]([C:9]#[N:10])[CH:5]=1)=[O:13]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 27376742-Fluoro-4-(trifluoromethyl)anilineHCID 27564323-Amino-5-fluorobenzonitrile

Produkt 1

HCID 66899075HCID 66899075, VerbindungAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 6.15 g (45.18 mmol) of 5-fluoro-3-cyanoaniline in 90 ml of tetrahydrofuran is stirred at ambient temperature under an argon atmosphere. 4.3 ml (36.14 mmol) of diphosgene are added dropwise then 30 ml (135.54 mmol) of triethylamine. After refluxing in the reaction mixture for 3 hours, a solution of 7.10 g (39.64 mmol) of 4-amino-3-fluorotrifluoromethylbenzene in 10 ml of tetrahydrofuran is slowly added. The reflux is maintained for an additional 2 hours. The medium is then stirred into 100 ml of water, then extracted with 100 ml of ethyl acetate. The organic phase is washed with 100 ml of a saturated sodium chloride solution, dried over magnesium sulphate and concentrated to dryness using a rotary evaporator. The solid residue obtained is recrystallized at high temperature in 90 ml of acetonitrile in order to give 10.35 g of 1-(2-fluoro-4-trifluoromethylphenyl)-3-(3-cyano-5-fluorophenyl)urea in the form of a cream solid.

Aufarbeitung

  1. temperatureAfter refluxing in the reaction mixture for 3 hours
  2. temperatureThe reflux is maintained for an additional 2 hours
  3. extractionextracted with 100 ml of ethyl acetate
  4. washThe organic phase is washed with 100 ml of a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness
  7. customa rotary evaporator
  8. customThe solid residue obtained
  9. customis recrystallized at high temperature in 90 ml of acetonitrile in order

Quellen und Nachweise

ORD-Eintrag
ord-0f50632ec1d1498c9434864b5c0910d8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367715B2

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